An efficient metal-free cascade reaction between 1-dibromovinyl-2-nitro-substituted arenes and secondary amines results in the formation of polycyclic pseudoindoxyls in a single step. The reaction mechanism leading to these fused ring systems was investigated, and is believed to involve the initial formation of nitroarylated ynamines/ynamides. These intermediates cycloisomerize towards N-alkenyl-tethered 2-aminoisatogens via a carbene intermediate as demonstrated by QTAIM (quantum theory of atoms in molecules) and ELF (electron localization function) analysis. A subsequent intramolecular dipolar cycloaddition afforded the title compounds.

Original languageEnglish
Pages (from-to)5660-5664
Number of pages5
JournalAngewandte Chemie International Edition
Issue number20
Publication statusPublished - 14 May 2018

    Research areas

  • cycloaddition, domino reactions, nitrogen heterocycles, ynamides, ynamines

ID: 39056653